[CH3:1][C:2]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]=[CH:9]1)([CH3:7])[CH2:3][CH2:4][CH2:5]O.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1(=[O:60])[NH:54][C:53](=[O:55])[C:52]2=[CH:56][CH:57]=[CH:58][CH:59]=[C:51]12>C1COCC1>[CH3:1][C:2]([N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[N:10]=[CH:9]1)([CH3:7])[CH2:3][CH2:4][CH2:5][N:54]1[C:50](=[O:60])[C:51]2[C:52](=[CH:56][CH:57]=[CH:58][CH:59]=2)[C:53]1=[O:55]To a solution of 4-methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentan-1-ol (1 eq) in THF (20 ml) was added dropwise diethyl azodicarboxylate (1.1 eq), triphenyl phosphine (1.1 eq), and pthalimide (1.1 eq). The yellow solution was stirred at room temperature overnight and the solution was concentrated. The crude product was directly purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA to yield 2-[4-methyl-4-(4-pyridin-3-yl-imidazol-1-yl)-pentyl]-isoindole-1,3-dione (66%). MH+(375)
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